Compounds with bridgehead nitrogen. 50—1H NMR spectra and structures of the products derived from the reaction between trans-3-aminotetralin-2-ol and formaldehyde

✍ Scribed by Trevor A. Crabb; Olive G. Roch; Paul Robinson

• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: English
• Weight: 389 KB
• Volume: 24
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260241209

✦ Synopsis

In contrast to the reported reaction between trans-l-aminotetralin-2-01 and formaldehyde, which gives r-6a, c-9a,t-15a,t-18a-5,6,6a,9a,14,15,15a,18a-o~ahy~o-9,18-me~~odinaphtho [ 1,2-d: 1',2'-i] [1,6,3,8]dioxadiazecine, an examination of the 6 4.0-5.0 region of the 'H NMR spectra of the products of the reaction between truns-3-aminotetralin-2-01 and formaldehyde showed these to be a 50 : 50 mixture of r-5a,t-Sa,c-14a,t-l7a-and r-5a,c-8a,t-14a,t-17a-5,5a,8a,9,14,14a,17a,l8-octahydro-8,17-methanodinaphtho[2,3-d : 2',3'-i][1,6,3,8]dioxadiazecine. In a similar way, the reaction between trans-2-aminocyclohexanol and formaldehyde was reexamined and found to produce initially a cu 80: 20 mixture of r-4a,t-7a,c-lla,t-l4a-and r-4a,c-7a,t-lla,t-14a-7,14-methanoperhydrodibenzo [ d, i ] [ 1,6,3, 81 dioxadiazecines.